HCID 58465939, compound → HCID 58465944, compound

HRID 1472404Notes

Reaction equation

HRID 1472404 reaction equation
[O:1]1[CH2:6][CH:5]=[C:4]([C:7]2[CH:20]=[C:19]([F:21])[C:18]3[O:17][C:16]4[C:11](=[CH:12][C:13]([C:22]5[C:23]([F:28])=[N:24][CH:25]=[CH:26][CH:27]=5)=[CH:14][CH:15]=4)[C@:10]4([N:33]=[C:32]([NH2:34])[CH2:31][O:30][CH2:29]4)[C:9]=3[CH:8]=2)[CH2:3][CH2:2]1.[H][H]>CCO.[Pd]>[F:21][C:19]1[C:18]2[O:17][C:16]3[C:11](=[CH:12][C:13]([C:22]4[C:23]([F:28])=[N:24][CH:25]=[CH:26][CH:27]=4)=[CH:14][CH:15]=3)[C@:10]3([N:33]=[C:32]([NH2:34])[CH2:31][O:30][CH2:29]3)[C:9]=2[CH:8]=[C:7]([CH:4]2[CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)[CH:20]=1

Participants

5

Reactant 2

HCID 58465939HCID 58465939, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 58465944HCID 58465944, compoundYield 71.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

In a microwave vial, (S)-2′-(3,6-dihydro-2H-pyran-4-yl)-4′-fluoro-7′-(2-fluoropyridin-3-yl)-2,6-dihydrospiro[[1,4]oxazine-3,9′-xanthen]-5-amine (0.040 g, 0.087 mmol) and Pd/C (10%, 0.055 g, 0.052 mmol) were suspended in EtOH (1.5 mL). A balloon full of hydrogen (˜1 L) was emptied into the vessel, venting through a needle, and the vessel was sealed. After 2 days, the mixture was filtered through Celite, rinsing with 5% MeOH-DCM. The filtrate was concentrated, and the residue was purified by chromatography (7.5% MeOH/DCM) to afford 29 mg of (S)-4′-fluoro-7′-(2-fluoropyridin-3-yl)-2′-(tetrahydro-2H-pyran-4-yl)-2,6-dihydrospiro[[1,4]oxazine-3,9′-xanthen]-5-amine

Workup

  1. customthe vessel was sealed
  2. filtrationthe mixture was filtered through Celite
  3. washrinsing with 5% MeOH-DCM
  4. concentrationThe filtrate was concentrated
  5. customthe residue was purified by chromatography (7.5% MeOH/DCM)

Sources & evidence

ORD record
ord-6808db5f9fb3410f846517fb42bb0513
Source dataset
uspto-grants-2015_04
Patent number
US09012446B2

Reaction notes

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